(3S)-3-<(benzyloxycarbonyl)amino>-1-bromo-5-methyl-2-oxohexane | 118252-77-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S)-3-<(benzyloxycarbonyl)amino>-1-bromo-5-methyl-2-oxohexane
• 英文别名: (3-bromo-1-(S)-(2-methylpropyl)-2-oxopropyl)carbamic acid benzyl ester；Cbz-leucyl bromomethane；(3S)-3-[(benzyloxycarbonyl)amino]-1-bromo-5-methyl-2-oxohexane；benzyl N-[(3S)-1-bromo-5-methyl-2-oxohexan-3-yl]carbamate
• CAS: 118252-77-0
• 化学式: C₁₅H₂₀BrNO₃
• 分子量: 342.233
• InChiKey: QCQADFVWBLBJOJ-ZDUSSCGKSA-N

物化性质

• 沸点：
  449.3±35.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S)-3-<(benzyloxycarbonyl)amino>-1-bromo-5-methyl-2-oxohexane 在 palladium on activated charcoal 氢气 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 (S)-3-methyl-1-(2-phenyl-1H-imidazol-4-yl)butan-1-amine
  参考文献：
  名称：

  Chiral imidazole derivatives synthesis from enantiopure N-protected α-amino acids

  摘要：

  A route to the preparation of enantiopure ligands based on a 2-phenylimidazol ring is described. The stereogenic centre is placed into the chain bonded to the fourth carbon of the imidazole ring. The synthesis starts from inexpensive and readily available N-protected alpha-amino acids, as the source of chirality, which are converted into appropriate alpha-diazoketones and, consequently, into alpha-bromoketones. These alpha-bromoketones are good precursors for reactions with amidines to provide the imidazole ring. The deprotection into the final products was carried out using hydrogen. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.049
• 作为产物：
  描述：

  N-苄氧羰基-L-亮氨酸 在 N-甲基哌啶 、 氢溴酸 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 0.17h， 生成 (3S)-3-<(benzyloxycarbonyl)amino>-1-bromo-5-methyl-2-oxohexane
  参考文献：
  名称：

  肾素抑制剂含有等位性取代连接P3和P2位的酰胺键。

  摘要：

  已经制备了具有13个连接P3和P2位置的不同等排体的肾素抑制剂。讨论了这些化合物表现出的合成途径和体外活性。两种最有效的化合物47和48包含羟乙烯等排物psi [CHOHCH2]，IC50值分别为61和22 nM。

  DOI：

  10.1021/jm00164a058

文献信息

• Inhibition of aminopeptidases by peptides containing ketomethylene and hydroxyethylene amide bond replacements
  作者：Scott L. Harbeson、Daniel H. Rich

  DOI：10.1021/jm00126a039

  日期：1989.6

  been prepared by the synthesis of peptide substrate analogues in which the scissile amide bond has been replaced with the hydrolytically stable ketomethylene (-COCH2-) and hydroxyethylene [-CH(OH)CH2-] functionalities. Two synthetic strategies were used to prepare the inhibitors, and the advantages and disadvantages of each are discussed. The synthesis of peptides that contain the hydroxyethylene isostere

  氨基肽酶的抑制剂是通过合成肽底物类似物制备的，其中易裂的酰胺键已被水解稳定的酮亚甲基（-COCH2-）和羟基乙烯[-CH（OH）CH2-]官能团取代。使用了两种合成策略来制备抑制剂，并讨论了每种策略的优缺点。竞争性的内酯和内酰胺的形成使含有羟乙烯等排异构体的肽的合成变得复杂，并且尝试制备游离的N-末端二肽羟乙烯等排异构体的尝试是不成功的。检查的所有酮亚甲基等位基因都是亮氨酸氨基肽酶和氨基肽酶M的弱抑制剂。但是，酮亚甲基抑制剂LysK（RS）Phe（58）（Ki = 4 nM）是与天然产物相当的有效抑制剂，arphamenine A（ArgKPhe; Ki = 2.5 nM）。在不存在镁离子的情况下，观察到正常的Michaelis-Menten动力学抑制膜亮氨酸氨基肽酶的动力学，但在存在Mg2 +的情况下获得了非线性动力学。
• Renin inhibitors containing isosteric replacements of the amide bond connecting the P3 and P2 sites
  作者：James S. Kaltenbronn、J. P. Hudspeth、E. A. Lunney、B. M. Michniewicz、E. D. Nicolaides、J. T. Repine、W. H. Roark、M. A. Stier、F. J. Tinney

  DOI：10.1021/jm00164a058

  日期：1990.2

  Renin inhibitors having 13 different isosteres connecting the P3 and P2 positions have been prepared. Synthetic routes and in vitro activity exhibited by these compounds are discussed. The two most potent compounds, 47 and 48, contained the hydroxyethylene isostere, psi [CHOHCH2], and had IC50 values of 61 and 22 nM, respectively.

  已经制备了具有13个连接P3和P2位置的不同等排体的肾素抑制剂。讨论了这些化合物表现出的合成途径和体外活性。两种最有效的化合物47和48包含羟乙烯等排物psi [CHOHCH2]，IC50值分别为61和22 nM。
• Peptidomimetics Through Click Chemistry: Synthesis of Novel β-Keto Triazole Acids from N-Protected Amino Acids
  作者：N. Narendra、T. M. Vishwanatha、Vommina V. Sureshbabu

  DOI：10.1007/s10989-010-9214-z

  日期：2010.12

  An efficient procedure for the preparation of azidomethylketones from N-urethane protected amino acids and their application in Cu(I) catalyzed azide-alkyne cycloaddition reaction are described. The synthesis has been carried out under mild conditions with all the commonly used urethane protected (Fmoc, Boc and Z) amino acids and the desired azides/triazoles were obtained in good yields. Incorporation of these triazole amino acids into small peptides generating dipeptidomimetics containing β-keto triazole units has also been demonstrated.

  描述了一种有效的程序，用于从N-氨基甲酸酯保护的氨基酸制备叠氮甲基酮及其在铜(I)催化的叠氮-炔烃环加成反应中的应用。该合成在温和条件下进行，适用于所有常用的氨基甲酸酯保护的氨基酸（Fmoc、Boc 和 Z），并以良好的产率获得了所需的叠氮化物/三唑化物。还展示了将这些三唑氨基酸纳入小肽中，生成含有β-酮三唑单元的二肽模仿物。
• Stereocontrolled Synthesis of Erythro N-Protected α-Amino Epoxides and Peptidyl Epoxides.
  作者：Amnon Albeck、Rachel Persky

  DOI：10.1016/s0040-4020(01)80651-7

  日期：1994.1

  N-protected α-amino epoxides of erythro configuration, derived from α-amino acids, were synthesized in a stereoselective manner. The erythro (2S,3S) configu- ration was achieved by the synthetic sequence: amino acid → haloketone → halohydrin → epoxide. A mechanistic explanation for the observed stereoselectivity is presented. This stereoselective synthetic approach was applied to the synthesis of a

  以立体选择性方式合成衍生自α-氨基酸的N-保护的赤型构型的α-氨基环氧化物。所述赤氨基酸→卤代酮→卤代醇环氧→：（2S，3S）configu-配给由合成序列来实现的。给出了对所观察到的立体选择性的机械解释。该立体选择性合成方法被用于合成具有预定的手性环氧化物部分的绝对构型的各种短肽基环氧化物。
• RADDATZ, PETER;SCHMITGES, CLAUS J.;MINCK, KLAUS OTTO
  作者：RADDATZ, PETER、SCHMITGES, CLAUS J.、MINCK, KLAUS OTTO

  DOI：——

  日期：——